EP4353327A1 - Composition de parfum - Google Patents

Composition de parfum Download PDF

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Publication number
EP4353327A1
EP4353327A1 EP22811170.4A EP22811170A EP4353327A1 EP 4353327 A1 EP4353327 A1 EP 4353327A1 EP 22811170 A EP22811170 A EP 22811170A EP 4353327 A1 EP4353327 A1 EP 4353327A1
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EP
European Patent Office
Prior art keywords
mass
formula
fragrance
compound represented
parts
Prior art date
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EP22811170.4A
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German (de)
English (en)
Inventor
Akari Saito
Hironori Mori
Jun Deguchi
Tsubasa Arai
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Kao Corp
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Kao Corp
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Publication of EP4353327A1 publication Critical patent/EP4353327A1/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/18—Peptides; Protein hydrolysates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment

Definitions

  • the present invention relates to a fragrance composition.
  • ⁇ -(2-Alkylcyclohexyloxy)- ⁇ -alkanols of which especially 1-(2-t-butylcyclohexyloxy)-2-alkanol, are useful fragrance materials that have a woody, amber-like aromatic odor, exhibit excellent persistence of odor, and can be produced at low cost ( JP 2013-151482A ).
  • 1-(2-t-butylcyclohexyloxy)-2-butanol is widely known as Amber Core, a fragrance that has woody and amber-like notes (Japanese cypress-like fresh odor) as well as long-term persistence of odor.
  • the present invention relates to a perfuming agent composed of a compound represented by Formula (I).
  • the inventors of the present invention have found that o-t-butyl cyclohexanone generated during the production of Amber Core and having a low boiling point is a component with an unpleasant odor.
  • certain types of ketal products have favorable fruity (apple-like), herbal, and minty odors by themselves. Further, they have found that, when such a ketal product is contained at a specific concentration in a composition containing Amber Core, it brings about an advantageous effect in that nectar-like sweetness and voluminousness of the odor are imparted to the Amber Core. Based on these findings, the inventors finally devised a perfuming agent and a fragrance composition according to the present invention.
  • JP S56(1981)-79686A discloses a ketal compound shown below. It has been reported that this compound has highly pungent, medicinal herb-like and fruity odors. However, there is a problem in that impressions of medicinal herb-like highly pungent and chemical odors are not widely usable in preparation of fragrance blends.
  • JP H6(1994)-305999A discloses a ketal compound shown below. It has been reported that this compound has fruity, green, woody, floral, anise-like, aromatic, camphor-like, and tobacco-like odors. However, there is a problem in that impressions of anise-like, camphor-like, and tobacco-like odors are not widely usable in preparation of fragrance blends.
  • the present invention relates to a perfuming agent composed of a compound represented by Formula (I).
  • the present invention also relates to a fragrance composition containing: a compound represented by Formula (II) and a compound represented by Formula (I), wherein a mass ratio between the compound represented by Formula (II) and the compound represented by Formula (I) (the compound represented by Formula (II) : the compound represented by Formula (I)) is 99.99:0.01 or more and 98:2 or less.
  • the perfuming agent composed of the compound represented by Formula (I) and the fragrance composition containing the perfuming agent according to the present invention have a favorable fruity (apple-like), herbal, and minty odor.
  • the fragrance composition containing the compound represented by Formula (II) and the compound represented by Formula (I) according to the present invention brings about an advantageous effect in that nectar-like sweetness and voluminousness of the odor are imparted to Amber Core.
  • the present invention relates to a perfuming agent composed of a compound represented by Formula (I).
  • the compound represented by Formula (I) can be produced by, for example, a method to be described below.
  • a compound of Formula (X) and a compound of Formula (XI) are heated under basic conditions (e.g., in the presence of sodium hydroxide) to obtain a compound of Formula (XII).
  • the compound of Formula (XII) is then hydrogenated in the presence of hydrogen using a specific catalyst (e.g., a palladium-containing catalyst), whereby a compound of Formula (I) can be obtained.
  • a specific catalyst e.g., a palladium-containing catalyst
  • the compound represented by Formula (I) can be produced by a conventionally known method such as, for example, a method performed using the same conditions as those described in JP 2013-151482A .
  • the present invention also relates to a fragrance composition containing: a compound represented by Formula (II) and a compound represented by Formula (I), wherein a mass ratio between the compound represented by Formula (II) and the compound represented by Formula (I) (the compound represented by Formula (II) : the compound represented by Formula (I)) is 99.99:0.01 or more and 98:2 or less. That is, the mass ratio between the compound represented by Formula (I) and the compound represented by Formula (II) [the compound represented by Formula (I)/the compound represented by Formula (II)] is 0.01/99.99 or more and 2/98 or less.
  • the mass ratio between the compound represented by Formula (II) and the compound represented by Formula (I) is preferably 99.97:0.03 or more and more preferably 99.95:0.05 or more from the viewpoint of imparting nectar-like sweetness and voluminousness of the odor to the compound represented by Formula (II), and is preferably 99:1 or less, more preferably 99.20:0.80 or less, and still more preferably 99.50:0.50 or less from the viewpoint of imparting an amber-like odor of the compound represented by Formula (II).
  • the mass ratio between the compound represented by Formula (II) and the compound represented by Formula (I) is preferably 99.99:0.01 or more and 99:1 or less, more preferably 99.97:0.03 or more and 99.20 : 0.80 or less, and still more preferably 99.95:0.05 or more and 99.50:0.50 or less from the viewpoint of imparting nectar-like sweetness and voluminousness of the odor to the compound represented by Formula (II).
  • the mass ratio between the compound represented by Formula (I) and the compound represented by Formula (II) is 0.01/99.99 or more and 1/99 or less, more preferably 0.03/99.97 or more and 0.80/99.2 or less, and still more preferably 0.05/99.95 or more and 0.50/99.50 or less from the viewpoint of imparting nectar-like sweetness and voluminousness of the odor to the compound represented by Formula (II).
  • the compound represented by Formula (II) can be produced by a conventionally known method such as, for example, the method described in JP H4(1992)-217937A .
  • the compound represented by Formula (II) can be produced by, for example, a method to be described below.
  • a compound of Formula (XIII) and a compound of Formula (XIV) are heated in the presence of a base (e.g., sodium hydroxide), whereby a compound of Formula (XV) can be obtained.
  • a base e.g., sodium hydroxide
  • the compound of Formula (XV) is then hydrogenated in the presence of a specific catalyst (e.g., a palladium catalyst) and hydrogen, whereby a compound of Formula (II) can be obtained.
  • a specific catalyst e.g., a palladium catalyst
  • the perfuming agent composed of the compound represented by Formula (I) according to the present invention has a favorable fruity (apple-like), herbal, and minty odor. Thus, it harmonizes well with various other fragrances and can bring about a characteristic effect on odors when used in fragrance blending.
  • the perfuming agent composed of the compound represented by Formula (I) according to the present invention can be used in combination with a fragrance(s) other than the compound represented by Formula (I), such as a commonly used other fragrance component or a fragrance blend having a desired composition.
  • a fragrance composition containing the perfuming agent composed of the compound represented by Formula (I) according to the present invention and a fragrance(s) other than the compound represented by Formula (I) is preferable, and also, a fragrance composition containing the perfuming agent composed of the compound represented by Formula (I) according to the present invention and a fragrance(s) other than the compounds represented by Formulae (I) and (II) is preferable.
  • a fragrance(s) other than the compound represented by Formula (I) in combination it is possible to impart, for example, a favorable fruity (apple-like), herbal, and minty odor to the fragrance composition of the present invention.
  • the fragrance composition containing the compounds represented by Formulae (I) and (II) according to the present invention nectar-like sweetness and voluminousness of the odor are imparted to the compound represented by Formula (II).
  • the fragrance composition containing the compounds represented by Formulae (I) and (II) according to the present invention can be used in combination with a commonly used other fragrance component or a fragrance blend having a desired composition as the fragrance(s) other than the compounds represented by Formulae (I) and (II).
  • a fragrance(s) other than the compounds represented by Formulae (I) and (II) in combination, it is possible to impart the odor of the compound represented by Formula (II) and nectar-like sweetness and voluminousness of the odor to the fragrance composition of the present invention. That is, the fragrance composition containing the compounds represented by Formulae (I) and (II) according to the present invention preferably further contains a fragrance(s) other than the compounds represented by Formulae (I) and (II).
  • fragrance components such as alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, carvones, lactones, nitriles, amines, Schiff bases, natural essential oils, and natural extracts (excluding the compound represented by Formula (I)).
  • the present invention relates to a fragrance composition containing: at least one substance that is other than compounds represented by Formulae (I) and (II) and is selected from alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts: and the perfuming agent according to the present invention.
  • the mass ratio between the perfuming agent composed of the compound represented by Formula (I) and a fragrance(s) other than the compounds represented by Formulae (I) and (II) (hereinafter simply referred to as the other fragrance(s)) (the compound represented by Formula (I)/the other fragrance(s)) is: preferably 0.01/99.99 or more, more preferably 0.1/99.9 or more, and still more preferably 1/99 or more from the viewpoint of allowing the perfuming agent to exhibit its function; preferably 1/2 or less, more preferably 1/3 or less, and still more preferably 1/4 or less from the same viewpoint; and preferably 0.01/99.99 or more and 1/2 or less, more preferably 0.1/99.9 or more and 1/3 or less, and still more preferably 1/99 or more and 1/4 or less.
  • the content of the perfuming agent composed of the compound represented by Formula (I) in the fragrance composition is as follows, from the viewpoint of allowing the perfuming agent to exhibit its function: preferably 0.01 mass% or more, more preferably 0.1 mass% or more, and still more preferably 0.2 mass% or more; preferably 20 mass% or less, more preferably 15 mass% or less, and still more preferably 10 mass% or less; and preferably 0.01 mass% or more and 20 mass% or less, more preferably 0.1 mass% or more and 15 mass% or less, and still more preferably 0.2 mass% or more and 10 mass% or less.
  • examples of the other fragrance(s) that can be used in combination with the compounds represented by Formulae (I) and (II) include fragrance components such as alcohols, hydrocarbons, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, carvones, lactones, nitriles, amines, Schiff bases, natural essential oils, and natural extracts (excluding the compounds represented by Formulae (I) and (II)).
  • those preferably used for the above-described fragrance composition are alcohols, phenols, esters, carbonates, aldehydes, ketones, acetals, ethers, lactones, nitriles, amines, natural essential oils, and natural extracts.
  • alcohols examples include aliphatic alcohols, terpene alcohols, aromatic alcohols, and other alcohols. Of these, aliphatic alcohols are preferable.
  • terpene alcohols examples include linalool, ethyl linalool, citronellol, hydroxycitronellol, geraniol, tetrahydrogeraniol, nerol, terpineol, ⁇ -terpineol, dihydromyrcenol, farnesol, nerolidol, cedrol, menthol, and borneol.
  • aromatic alcohols examples include phenylethyl alcohol, benzyl alcohol, dimethyl benzyl carbinol, phenylethyl dimethyl carbinol, and phenyl hexanol.
  • Examples of the aliphatic alcohols include cis-3-hexenol, 1-(2,2,6-trimethylcyclohexy)-3-hexanol, Sandahnysore Core (trade name, Kao Corporation, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol), Amber Core (trade name, Kao Corporation, 1-(2-t-butylcyclohexyloxy)-2-butanol), Magnol (trade name, Kao Corporation, a mixture containing ethyl norbornyl cyclohexanol as a main component), Undecavertol (trade name, Givaudan, 4-methyl-3-decen-5-ol), isobornyl cyclohexanol, and Terpirosa (trade name, Kao Corporation, 3,6-dimethyl-2-heptanol). It is to be noted here that, for "the fragrance composition containing the compounds represented by Formulae (I
  • glycols such as dipropylene glycol, Florosa (trade name, Givaudan, chemical name: 4-methyl-2-(2-methylpropyl)tetrahydro-2H-4-pyranol), maltol, and ethyl maltol.
  • hydrocarbons examples include limonene, ⁇ -pinene, ⁇ -pinene, terpinen, cedrene, longifolene, and valencene.
  • phenols examples include guaiacol, eugenol, dihydroeugenol, isoeugenol, thymol, para-cresol, vanillin, and ethyl vanillin.
  • esters examples include aliphatic carboxylic acid esters, aromatic carboxylic acid esters and other carboxylic acid esters.
  • Examples of aliphatic carboxylic acids that form the aliphatic carboxylic esters include straight-chain and branched carboxylic acids having 1 to 18 carbon atoms. Of these, carboxylic acids having 1 to 6 carbon atoms, such as formic acid, acetic acid, and propionic acid are important, and in particular, acetic acid is important.
  • Examples of aromatic carboxylic acids that form the aromatic carboxylic esters include benzoic acid, anisic acid, phenylacetic acid, cinnamic acid, salicylic acid, and anthranilic acid.
  • Examples of alcohols that form the aliphatic and aromatic esters include straight-chain and branched aliphatic alcohols having 1 to 5 carbon atoms and the alcohols described above as examples of the fragrance components.
  • Examples of formic acid esters include linalyl formate, citronellyl formate, and geranyl formate.
  • acetic acid esters include ethyl acetate, isoamyl acetate (isopentyl acetate), benzyl acetate, hexyl acetate, phenyl acetate, p-cresyl acetate, cis-3-hexenyl acetate, linalyl acetate, citronellyl acetate, geranyl acetate, neryl acetate, terpinyl acetate, nopyl acetate, bornyl acetate, isobornyl acetate, acetyl eugenol, acetyl isoeugenol, o-tert-butylcyclohexyl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl acetate, phenylethyl acetate, styralyl acetate, cinnamyl
  • propionic acid esters examples include ethyl propionate, citronellyl propionate, tricyclodecenyl propionate, benzyl propionate, styralyl propionate, and Helvetolide (trade name, Firmenich, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methylpropyl)propionate).
  • butyric acid esters include citronellyl butyrate, dimethylbenzylcarbinyl n-butyrate, isoamyl n-butyrate, and n-amyl n-butyrate; and examples of isobutyric acid esters include tricyclodecenyl isobutyrate and phenoxyethyl isobutyrate.
  • valeric acid esters examples include methyl valerate, ethyl valerate, butyl valerate, amyl valerate, benzyl valerate, and phenylethyl valerate; and examples of hexanoic acid esters include methyl hexanoate, ethyl hexanoate, allyl hexanoate, linalyl hexanoate, and citronellyl hexanoate.
  • heptanoic acid esters examples include methyl heptanoate and allyl heptanoate.
  • nonenoic acid esters examples include methyl 2-nonenoate, ethyl 2-nonenoate, and ethyl 3-nonenoate.
  • benzoic acid esters examples include methyl benzoate, benzyl benzoate, and 3,6-dimethyl benzoate.
  • cinnamic acid esters examples include methyl cinnamate and benzyl cinnamate.
  • salicylic acid esters examples include methyl salicylate, n-hexyl salicylate, cis-3-hexenyl salicylate, cyclohexyl salicylate, and benzyl salicylate.
  • brassylic acid esters examples include ethylene brassylate.
  • tiglic acid esters examples include geranyl tiglate, 1-hexyl tiglate, and cis-3-hexenyl tiglate.
  • jasmonic acid esters examples include methyl jasmonate; and examples of dihydrojasmonic acid esters include MDJ (trade name, Kao Corporation, methyl dihydrojasmonate, methyl (2-pentyl-3-oxocyclopentyl)acetate).
  • glycidic acid esters examples include methyl 2,4-dihydroxy-ethyl methyl phenyl glycidate and 4-methyl phenyl ethyl glycidate.
  • anthranilic acid esters examples include methyl anthranilate, ethyl anthranilate, and dimethyl anthranilate.
  • glycolic acid esters examples include allylcyclohexyl glycolate.
  • esters examples include Ethyl Safranate (trade name, Givaudan, ethyl dihydrocyclogelanate), Poirenate (trade name, Kao Corporation, ethyl-2-cyclohexyl propionate), Fruitate (trade name, Kao Corporation, ethyl tricyclo[5.2.1.0 2.6 ]decane-2-carboxylate), ethyl acetoacetate, Fructone (trade name, IFF, ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate), Manzanate (trade name, Givaudan, ethyl 2-methylpentanoate), ethyl 2-methylbutyrate, and allyl cyclohexylpropionate.
  • Ethyl Safranate trade name, Givaudan, ethyl dihydrocyclogelanate
  • Poirenate trade name, Kao Corporation, ethyl-2-cyclohexyl
  • Examples of the carbonates include Liffarome (trade name, IFF, cis-3-hexenyl methyl carbonate), Jasmacyclat (trade name, Kao Corporation, methyl-cyclooctyl carbonate), and Floramat (trade name, Kao Corporation, ethyl-2-t-butylcyclohexyl carbonate).
  • aldehydes examples include n-octanal, n-nonanal, n-decanal, n-dodecanal, 2-methylundecanal, 10-undecenal, citronellal, citral, hydroxycitronellal, Triplal (trade name, IFF, 2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde), Cyclovertal (trade name, Kao Corporation, dimethyl-3-cyclohexenyl-1-carboxaldehyde), benzaldehyde, phenylacetaldehyde, phenylpropyl aldehyde, cinnamic aldehyde, dimethyltetrahydrobenzaldehyde, Bourgeonal (trade name, Givaudan, 3-(4-tert-butylphenyl)propanal), Lyral (trade name, IFF, hydroxy myrac aldehyde), Pollenal II (trade name,
  • ketones examples include methylheptenone, dimethyloctenone, 3-octanone, hexylcyclopentanone, dihydrojasmone, Veloutone (trade name, Firmenich, 2,2,5-trimethyl-5-pentylcyclopentanone), Nectaryl (trade name, Givaudan, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone), ionone, ⁇ -ionone, methyl ionone, methyl ionone-G, ⁇ -methyl ionone, damascene, ⁇ -damascone, ⁇ -damascone, ⁇ -damascone, Isodamascone (trade name, Symrise, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone), damascenone, Dynascone (trade name, Firmenich, 1-(5,5-dimethyl-1-cyclo
  • acetals examples include acetaldehyde ethylphenylpropyl acetal, citral diethyl acetal, phenylacetaldehyde glyceryl acetal, ethyl acetoacetate ethylene glycol acetal, Boisambrene Forte (trade name, Kao Corporation, ethoxymethyl cyclododecyl ether), Troenan (trade name, Kao Corporation, 5-methyl-5-propyl-2-(1-methylbutyl)-1,3-dioxane), Floropal (trade name, Symrise, 2,4,6-trimethyl-4-phenyl-1,3-dioxane), and Magnolan (trade name, Symrise, 2,4-dimethyl-4,4a,5,9b-tetrahydroindeno[1,2-d][1,3]dioxane).
  • ethers examples include cedryl methyl ether, estragole, anethole, ⁇ -naphthyl methyl ether, ⁇ -naphthyl ethyl ether, limonene oxide, rose oxide, nerol oxide, 1,8-cineole, rose furan, Ambroxan (trade name, Kao Corporation, [3aR-(3a ⁇ ,5a ⁇ ,9a ⁇ ,9b ⁇ )]dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan), Herbavert (trade name, Kao Corporation, 3,3,5-trimethylcyclohexyl ethyl ether), Galaxolide (trade name, IFF, hexamethylhexahydrocyclopentabenzopyran), and phenylacetaldehyde dimethylacetal.
  • Ambroxan trade name, Kao Corporation, [3aR-(3a ⁇ ,5a ⁇
  • carboxylic acids examples include benzoic acid, phenylacetic acid, cinnamic acid, hydrocinnamic acid, butyric acid, and 2-hexenoic acid.
  • lactones examples include ambrettolide, ⁇ -decalactone, ⁇ -decalactone, ⁇ -valerolactone, ⁇ -nonalactone, ⁇ -undecalactone, 6-hexalactone, ⁇ -jasmolactone, whisky lactone, coumarin, cyclopentadecanolide, cyclohexadecanolide, 11-oxahexadecanolide, and butylidene phthalide.
  • nitriles examples include tridecene-2-nitrile, geranyl nitrile, citronellyl nitrile, and dodecanenitrile.
  • Examples of the amines include indole, skatole, 6-methylquinoline, 6-isopropylquinoline, and isobutylquinoline.
  • Schiff bases examples include aurantiol and ligantraal.
  • oils examples include oils, concretes, absolutes, resinoids, oleoresins, tinctures, immersion liquids, and balsams of natural raw materials, such as orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, galbanum, chamomile, rosemary, eucalyptus, sage, basil, rose, rockrose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamon, cedar, Japanese cypress, vetiver, patchouli, hay, lemongrass, labdanum, grapefruit, and elemi oils.
  • natural raw materials such as orange, lemon, lime, bergamot, vanilla, mandarin, peppermint, spearmint, lavender, galbanum, chamomile, rosemary, eucalyptus, sage, basil, rose, rockrose, geranium, jasmine, ylang-ylang, anise, clove,
  • the contents of these other fragrances can be selected as appropriate according to, for example, the type of fragrance blend and the type and intensity of intended aromatic odor.
  • the content of each of these other fragrances in a composition containing the fragrance composition of the present invention is preferably 0.0001 mass% or more and more preferably 0.001 mass% or more and is preferably 99.99 mass% or less and more preferably 80 mass% or less.
  • the total content of the other fragrances in a composition containing the fragrance composition of the present invention is preferably 5 mass% or more and more preferably 50 mass% or more and is preferably 99.99 mass% or less and more preferably 99.95 mass% or less.
  • the mass ratio between the total amount of the compounds represented by Formulae (I) and (II) and the above-described other fragrance(s) is: preferably 0.01/99.99 or more, more preferably 0.1/99.9 or more, and still more preferably 1/99 or more from the viewpoint of allowing the perfuming agent to exhibit its function; preferably 1/2 or less, more preferably 1/3 or less, and still more preferably 1/4 or less from the same viewpoint; and preferably 0.01/99.99 or more and 1/2 or less, more preferably 0.1/99.9 or more and 1/3 or less, and still more preferably 1/99 or more and 1/4 or less.
  • the content of the compound represented by Formula (I) in the fragrance composition is as follows, from the viewpoint of allowing the perfuming agent to exhibit its function: preferably 0.01 mass% or more, more preferably 0.1 mass% or more, and still more preferably 0.2 mass% or more; preferably 20 mass% or less, more preferably 15 mass% or less, and still more preferably 10 mass% or less; and preferably 0.01 mass% or more and 20 mass% or less, more preferably 0.1 mass% or more and 15 mass% or less, and still more preferably 0.2 mass% or more and 10 mass% or less.
  • the fragrance composition of the present invention may be used in combination with an oil that serves as a base and itself is odorless.
  • an oil allows fragrance components to be uniformly mixed together and to be easily added to a product, thereby allowing an odor with a moderate intensity to be more easily imparted to the product.
  • the oil include: polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, and dipropylene glycol; esters such as isopropyl myristate, dibutyl adipate, and diethyl sebacate; hydrocarbons such as liquid paraffin and squalane; and surfactants such as polyoxyethylene alkyl ethers and sorbitan fatty acid esters.
  • polyhydric alcohols and esters are preferable as the oil from the viewpoint of solubility of all the fragrance components, and dipropylene glycol and isopropyl myristate are more preferable.
  • the content of such an oil in the fragrance composition is preferably 0.01 mass% or more, more preferably 1 mass% or more, and still more preferably 5 mass% or more and is preferably 95 mass% or less, more preferably 90 mass% or less, and still more preferably 80 mass% or less.
  • the present invention further provides a cleaning composition containing the fragrance composition of the present invention, a cosmetic containing the fragrance composition of the present invention, and a fiber treating composition containing the fragrance composition of the present invention.
  • the cleaning composition of the present invention is preferably a body cleaning composition, a cleaning composition for clothing, or a cleaning composition for hard surfaces, more preferably a body cleaning composition or a cleaning composition for clothing, and still more preferably a cleaning composition for clothing.
  • the body cleaning composition is, for example, a skin cleaning composition, a hair cleaning composition, or a soap composition, and is preferably a skin cleaning composition.
  • the cleaning composition for hard surfaces is, for example, an all-purpose cleaner or a cleaning composition for tableware.
  • the fiber treating composition of the present invention is preferably a fabric softener composition.
  • the cosmetic of the present invention is preferably a perfume, a milky lotion, a skin lotion, or a sunscreen, and more preferably a perfume.
  • the cleaning composition of the present invention preferably contains an anionic surfactant in addition to the fragrance composition of the present invention, and may further contain a nonionic surfactant, a pH adjuster, a viscosity modifier, a solvent, an oil, an antiseptic agent, water, etc.
  • the fiber treating composition of the present invention preferably contains a cationic surfactant in addition to the fragrance composition of the present invention, and may further contain a pH adjuster, a solvent, an oil, an antiseptic agent, water, etc.
  • the perfume of the present invention may contain a solvent, water, or the like, in addition to the fragrance composition of the present invention.
  • the perfuming agent composed of the compound represented by Formula (I) and the fragrance composition containing the perfuming agent according to the present invention have a favorable fruity (apple-like), herbal, and minty odor. Further, the fragrance composition containing the compounds represented by Formulae (I) and (II) according to the present invention can create a new impression by imparting nectar-like sweetness and voluminousness of the odor to Amber Core.
  • the present invention relates to a method of using the perfuming agent of the present invention or the fragrance composition of the present invention ("the fragrance composition containing the perfuming agent composed of the compound represented by Formula (I) according to the present invention” and “the fragrance composition containing the compounds represented by Formulae (I) and (II) according to the present invention”) as a fragrance-imparting component, and more specifically to a method of using the same as a fragrance-imparting component in a fragrance composition, a cleaning composition, a cosmetic, or a fiber treating composition.
  • the cleaning composition is preferably a body cleaning composition, a cleaning composition for clothing, or a cleaning composition for hard surfaces, more preferably a body cleaning composition or a cleaning composition for clothing, and still more preferably a cleaning composition for clothing.
  • the body cleaning composition is, for example, a skin cleaning composition, a hair cleaning composition, or a soap composition, and is preferably a skin cleaning composition.
  • the cleaning composition for hard surfaces is, for example, an all-purpose cleaner or a cleaning composition for tableware.
  • the cosmetic is preferably a perfume.
  • the fiber treating composition is preferably a fabric softener composition.
  • the fragrance composition of the present invention is used in an amount of preferably 0.0001 mass% or more and more preferably 0.001 mass% or more, and preferably 30 mass% or less, more preferably 20 mass% or less, still more preferably 10 mass% or less, 1 mass% or less, and even more preferably 0.1 mass% or less, with respect to the cleaning composition, the cosmetic, or the fabric softener composition.
  • the fragrance composition in an amount falling within such a range is formulated as a fragrance material to be blended with other components, it can create a new impression by causing a citrus-like top note having sparkling and lively impressions and also adding green and woody nuances to a floral odor, thus imparting naturalness as if in a flower shop to the floral odor.
  • the fragrance composition of the present invention may be used in combination with an oil that itself is odorless.
  • the oil is the same as that described above in connection with the fragrance composition.
  • the fragrance composition of the present invention may further contain, as another fragrance(s), a commonly used other fragrance component or a fragrance blend having a desired composition. Such other fragrances are the same as those described above in connection with the fragrance composition.
  • the present invention includes the following embodiments.
  • the mass of a catalyst refers to the mass of the catalyst in a dry state.
  • DB-WAX capillary column, polyethylene glycol, inner diameter: 0.25 mm, length: 30 m, film thickness: 0.25 ⁇ m, Agilent Technologies, Inc.
  • 2-t-Butylphenol (1) (FUJIFILM Wako Pure Chemical Corporation, 350 g) and 35 g of 48% sodium hydroxide aqueous solution (Kanto Chemical Co., Inc.) were added to a 1-liter round-bottom flask provided with a Dimroth condenser and a dropping funnel in a nitrogen stream, and the resultant mixture was heated to 80°C.
  • 1,2-Butylene oxide (2) (Tokyo Chemical Industry Co., Ltd., 176 g) was added dropwise thereto over about 2 hours, followed by stirring at 80°C for 5 hours. After cooling the reaction mixture, an organic layer was separated from the underlying sodium hydroxide aqueous solution and then distilled, whereby 1-(2-t-butylphenyloxy)-2 butanol (3) was obtained in a yield of 96%.
  • the odor of each of the fragrance compositions obtained in Examples 2 to 9 and Comparative Example 1 were evaluated by three expert panelists. The evaluation was made using a fragrance test paper (Daimonji Paper Co., Ltd., 150 mm ⁇ 7 mm). The fragrance compositions of Examples 1 to 9 and Comparative Example 1, which differ from each other in the ratio of the isomers, were each applied to the tip of the fragrance test paper, and the evaluation was performed indoor after one hour. Sensory evaluation was made in terms of odor characteristics and odor intensity. The odor characteristics and odor intensity were relatively evaluated on a scale of 1 to 5, with higher numbers representing better results. For odor persistence, how many days the odor would last was examined, and the number of days the odor had lasted was recorded. In the sensory evaluation, the three expert panelists also described how they had felt about the quality and characteristics of the overall odor. The results obtained are shown in Table 1.
  • Example 1 The evaluation of the odor of the fragrance composition obtained in Example 1 (6-t-butyl-2-ethyl-1,4-dioxaspiro[4,5]decane alone) revealed that this fragrance composition had a favorable aromatic odor as a fragrance with fruity, apple-like, and nectar-like sweetness together with slightly herbal, minty, and woody aspects. None of the panelists perceived a pungent chemical odor or a tobacco- or leather-like aromatic odor, and this confirmed that this fragrance composition is widely usable in preparation of fragrance blends. [Table 1] Compound (4) : compound (5) mass ratio Amber, woody characteristics Sweetness Voluminousness Odor evaluation (by three expert panelists) Comp. Ex.
  • the term "voluminousness” means the intensity, profoundness, and richness of odors, and it is thus preferable for a fragrance to have voluminousness.
  • the fragrance compositions of the present invention each exhibited an effect of imparting nectar-like sweetness and voluminousness of the odor while maintaining a strong amber-like, woody, and slight camphor-like aromatic odor.
  • 6-t-Butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added to 900 parts by mass of a jasmine-note fragrance blend with the following composition, and the resulting composition was subjected to sensory evaluation.
  • the sensory evaluation was performed in the same manner as in Examples 1 to 9 and Comparative Example 1.
  • the results obtained are shown in Table 4.
  • the degree of effectiveness was relatively evaluated on a scale of 1 to 5, with higher numbers representing better results.
  • Ex. 2 900 parts by mass 100 parts by mass - 1000 parts by mass
  • Ex. 10 900 parts by mass - 100 parts by mass 1000 parts by mass [Table 4] ⁇ Results of Sensory Evaluation> Floral odor Odor evaluation (by three expert panelists) Comp.
  • Ex. 2 3 The composition has a jasmine-like floral odor, but lacks in naturalness and voluminousness of the overall odor.
  • Ex. 10 5 The composition has a jasmine-like floral odor with nectar-like sweetness added, and the overall odor is in harmony. White floral top and middle notes are emphasized, and the naturalness and the voluminousness of the overall odor are enhanced.
  • the results of the sensory evaluation by the three expert panelists revealed that the fragrance composition of the present invention imparted nectar-like sweetness to the jasmine-like fragrance blend and enhanced the naturalness and the voluminousness of the overall odor.
  • 6-t-Butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added to 925 parts by mass of a pear-note fragrance blend with the following composition, and the resulting composition was subjected to sensory evaluation.
  • the sensory evaluation was performed in the same manner as in Examples 1 to 10 and Comparative Examples 1 and 2.
  • the results obtained are shown in Table 7.
  • the degree of effectiveness was relatively evaluated on a scale of 1 to 5, with higher numbers representing better results.
  • composition has a pear-like fruity odor, but lacks in naturalness and voluminousness of the overall odor.
  • composition has a pear-like fruity odor with emphasis on a pear-like green odor and a fruity odor, and the naturalness and the voluminousness of the overall odor are enhanced.
  • 6-t-Butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added to 970 parts by mass of a lime-note fragrance blend with the following composition, and the resulting composition was subjected to sensory evaluation.
  • the sensory evaluation was performed in the same manner as in Examples 1 to 11 and Comparative Examples 1 to 3.
  • the results obtained are shown in Table 10.
  • the degree of effectiveness was relatively evaluated on a scale of 1 to 5, with higher numbers representing better results.
  • Ex. 4 970 parts by mass 30 parts by mass - 1000 parts by mass
  • Ex. 12 970 parts by mass - 30 parts by mass 1000 parts by mass [Table 10] ⁇ Results of Sensory Evaluation> Citrus odor Odor evaluation (by three expert panelists) Comp.
  • Ex. 4 3 The composition has a lime-like citrus odor, but its green odor is weak and it lacks in balance and naturalness.
  • Ex. 12 5 The composition has a lime-like citrus odor with emphasis on a lime-like green odor. The overall odor is in harmony, and has naturalness imparted thereto.
  • the results of the sensory evaluation by the three expert panelists revealed that the fragrance composition of the present invention emphasized the lime-like green odor, brought the overall odor into harmony, and imparted naturalness to the lime-like fragrance blend.
  • 6-t-Butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added to 950 parts by mass of a rose-note fragrance blend with the following composition, and the resulting composition was subjected to sensory evaluation.
  • the sensory evaluation was performed in the same manner as in Examples 1 to 12 and Comparative Examples 1 to 4.
  • the results obtained are shown in Table 13.
  • the degree of effectiveness was relatively evaluated on a scale of 1 to 5, with higher numbers representing better results.
  • Ex. 5 950 parts by mass 50 parts by mass - 1000 parts by mass
  • Ex. 13 950 parts by mass - 50 parts by mass 1000 parts by mass [Table 13] ⁇ Results of Sensory Evaluation> Floral odor Odor evaluation (by three expert panelists) Comp.
  • Ex. 5 3 The composition has a rose-like floral odor, but lacks in naturalness and voluminousness of the overall odor.
  • Ex. 13 5 The composition has a rose-like floral odor with sweetness imparted thereto, and rosy-tone naturalness and voluminousness of the overall odor are enhanced.
  • 6-t-Butyl-2-ethyl-1,4-dioxaspiro[4,5]decane (5) obtained in Reference Example 3 was added to 900 parts by mass of a lychee-note fragrance blend with the following composition, and the resulting composition was subjected to sensory evaluation.
  • the sensory evaluation was performed in the same manner as in Examples 1 to 13 and Comparative Examples 1 to 5.
  • the results obtained are shown in Table 16.
  • the degree of effectiveness was relatively evaluated on a scale of 1 to 5, with higher numbers representing better results.
  • Ex. 6 900 parts by mass 100 parts by mass - 1000 parts by mass
  • Ex. 14 900 parts by mass - 100 parts by mass 1000 parts by mass [Table 16] ⁇ Results of Sensory Evaluation> Fruity odor Odor evaluation (by three expert panelists) Comp.
  • Ex. 6 3 The composition has a lychee-like fruity odor, but has poor emanation of the odor and lacks sweetness and voluminousness of the overall odor.
  • Ex. 14 5 The composition has a lychee-like fruit odor with emphasis on emanation of a lychee-like odor and on a green odor. Fruit flesh-like sweetness is enhanced, and voluminousness is imparted to the odor.
  • the results of the sensory evaluation by the three expert panelists revealed that the fragrance composition of the present invention emphasized emanation of the odor and imparted sweetness and voluminousness of the odor to the lychee-like fragrance blend.
  • the perfuming agent containing the compound represented by Formula (I) and the fragrance composition containing the perfuming agent according to the present invention can provide fragrance compositions with a favorable fruity (apple-like), herbal, and minty odor. Further, the fragrance composition containing the compounds of Formulae (I) and (II) imparts nectar-like sweetness and voluminousness of the odor to Amber Core.

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EP22811170.4A 2021-05-24 2022-05-13 Composition de parfum Pending EP4353327A1 (fr)

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